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225916

Sigma-Aldrich

Benzylmagnesium chloride solution

2.0 M in THF

Synonym(s):

(Phenylmethyl)magnesium chloride, Benzylchloromagnesium, Chloro(phenylmethyl)magnesium

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About This Item

Linear Formula:
C6H5CH2MgCl
CAS Number:
6921-34-2
Molecular Weight:
150.89
Beilstein:
878506
MDL number:
MFCD00000469
UNSPSC Code:
12352103
PubChem Substance ID:
24853532
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in THF

density

1.031 g/mL at 25 °C

SMILES string

Cl[Mg]Cc1ccccc1

InChI

1S/C7H7.ClH.Mg/c1-7-5-3-2-4-6-7;;/h2-6H,1H2;1H;/q;;+1/p-1

InChI key

NRAFPLGJPPJUNB-UHFFFAOYSA-M

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General description

Benzylmagnesium chloride is an organometallic compound that acts as a Lewis acid and a strong base.

Application

Benzylmagnesium chloride (Grignard reagent) can be used as an alkylating reagent:
  • For alkylating quinolyl-functionalized Cp−chromium(III) complexes which are used as precursors for the preparation of active olefin polymerization catalysts.
  • In the synthesis of 2,3-disubstituted benzopyran-4-ones, 6-chloro-8-methylpurine derivative, and phenylalanine derivatives.

Signal Word

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dichotomy in regioselective cross-coupling reactions of 6, 8-dichloropurines with phenylboronic acid and methylmagnesium chloride: synthesis of 6, 8-disubstituted purines
Hocek M, et al.
Synthesis, 2004(06), 889-894 (2004)
Quinolyl-functionalised Cp-chromium polymerisation catalysts: synthesis and crystal structures of alkylation products
Enders M, et al.
Journal of Organometallic Chemistry, 687(1), 125-130 (2003)
A novel synthesis of 2, 3-disubstituted benzopyran-4-ones and application to the solid phase
Harikrishnan LS and Showalter HD H
Tetrahedron, 56(4), 515-519 (2000)
A facile three-step synthesis of 1, 2-amino alcohols using the Ellman homochiral tert-butylsulfinamide
Barrow JC, et al.
Tetrahedron Letters, 42(11), 2051-2054 (2001)
Oleg V Larionov et al.
Organic letters, 16(3), 864-867 (2014-01-15)
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method

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